CN1151719C - Disinfectant - Google Patents

Abstract

A disinfectant comprising at least one quaternary ammonium salt represented by the following general formula (1): wherein R1 represents an alkyl group of 8-14 carbon atoms, R2 and R3 each represent an alkyl group of 1-2 carbon atoms, and (B) represents two monovalent inorganic or organic anion groups or one divalent inorganic or organic anion group. The disinfectant has excellent bacteriocidal activity and is suitable as a disinfectant for medical care and working areas.

Description

Disinfectant

Background of the present invention

1 invention field

The present invention relates to the disinfectant of a kind of medical treatment and operation field purposes, this disinfectant is based on a kind of compound with bactericidal activity of novelty, and this disinfectant can replace benzalkonium chloride and didextrose acid chlohexidine to use.

The explanation of 2 correlation techniques

Common disinfectants comprises the oxirane of gas type etc., the glutaraldehyde of aldehydes type etc., the ethanol of pure type etc., the hydrogen peroxide of peroxide type etc., the tincture of iodine of iodine type, iodoform etc., the hypochlorous acid of chlorine compound type, chloramines etc., and the phenol soap of phenols type etc.But, all these disinfectants have the shortcoming that comprises stink, excitant and toxicity, and to the effect of container and utensil, therefore, are necessary to use them rightly according to its different application target.Such as the amphoteric surfactant of the quaternary ammonium salt of benzalkonium chloride, all example hydrochloric acid alkyl diaminoethyl glycine with extensively be used in the different field such as the biguanides framework compound of didextrose acid chlohexidine, this is odorlesses because of them, and excitant and toxicity are lower, effect to container and utensil is also minimum, also has gratifying bactericidal action (original text is bacterial action).Particularly biguanides skeleton disinfectant SY 1007 is used widely because of it has excellent bactericidal action, also Just because of this, it is found that many antibody-resistant bacterium that disinfectant had tolerance.As seen in hospital infection (hospital infection) problem that causes by MRSA (staphylococcus aureus of methicillin-resistant) to, the infection at random that causes of the such drug-resistant bacteria of cause is not all the more a kind of risk.

With benzalkonium chloride or salt dialkylaminobenzoic acid diaminoethyl glycine by comparison, it is more frequent that the bacterial strain of anti-didextrose acid chlohexidine occurs, however, people do not find a kind of better disinfectant as yet.

The present invention's general introduction

One of the object of the invention provides a kind of disinfectant that contains quarternary ammonium salt compound, the bactericidal action that this disinfectant had is more outstanding than benzalkonium chloride, salt dialkylaminobenzoic acid diaminoethyl glycine or didextrose acid chlohexidine, and this disinfectant is applicable to medical treatment and operation field.

For addressing the above problem, the inventor finds that through conscientiously research the quaternary ammonium salt that has two cation groups in the compound has strong bactericidal activity, has finished the present invention on this basis.

That is to say, the invention provides a kind of disinfectant, this disinfectant contains at least a quaternary ammonium salt by following general formula (1) representative:

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂And R ₃Represent the 1-2 carbon atom alkyl separately, [B] represents the inorganic or organic anion group of the inorganic of two monovalencies or an organic anion group or a divalence.

Brief description of drawings

Fig. 1 is for the compound that obtained by embodiment 1 ¹The H-NMR wave spectrum.

Fig. 2 is for the compound that obtained by embodiment 3 ¹The H-NMR wave spectrum.

Fig. 3 is for the compound that obtained by embodiment 36 ¹The H-NMR wave spectrum.

Fig. 4 is for the compound that obtained by embodiment 53 ¹The H-NMR wave spectrum.

To explanation preferred embodiment

Inorganic or organic anion group [B] preferably can be sulfate ion, phosphate anion, orthophosphite ions, hypophosphite ion, nitrate ion, nitrite ion, chloranion, chlorition, hypochlorite ion or by arbitrary anionic group of following general formula (2)-(8) representative according to the present invention:

2[X ^-] (2)

Wherein X represents chlorine atom, bromine atoms or iodine atom;

2[R ₄COO ^-] (3)

R wherein ₄Represent 1-7 carbon atom alkyl or alkenyl, this alkyl or alkenyl can have a hydroxyl or carbonyl;

[ ^-OCO-R ₅-COO ^-] (4)

R wherein ₅Represent direct key or 1-8 carbon atom alkylidene or alkenylene, this alkylidene or alkenylene can have a hydroxyl;

Each R wherein ₆Represent the 1-8 carbon atom alkyl, the phosphate anion can be simple monoesters or diester, or the mixture of the two;

Each R wherein ₇Represent the 1-8 carbon atom alkyl, the phosphate anion can be simple monoesters or diester, or the mixture of the two;

2[R ₈SO ₄] (7)

R wherein ₈Represent the 1-2 carbon atom alkyl;

R wherein ₉And R ₁₀Represent hydrogen atom, methyl or carboxyl separately.

According to the quaternary ammonium salt by above-mentioned general formula (1) representative of the present invention, the quaternizing agent that can be by making following general formula (9) and the reactive tertiary amine of following general formula (10) are prepared.

Wherein X represents chlorine atom, bromine atoms or iodine atom;

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂And R ₃Represent the 1-2 carbon atom alkyl separately.

Examples of compounds as above-mentioned general formula (9), can relate to halogenated compound, as α, α-two chloro-paraxylene, α, α-two chloro-meta-xylene, α, α-two chloro-ortho-xylene, α, α-two bromo-paraxylene, α, α-two bromo-meta-xylene, α, α-two bromo-ortho-xylene, α, α-two iodo-paraxylene, α, α-two iodo-meta-xylene, α, α-two iodo-ortho-xylene.Tertiary amine example as above-mentioned general formula (10), can relate to N, N-dimethyl octylame, N, N-dimethyl nonyl amine, N, N-dimethyl decyl amine, N, N-dimethyl undecylamine, N, N-dimethyl lauryl amine, N, N-dimethyl tridecyl amine, N, N-dimethyl tetradecy lamine, N, N-diethyl octylame, N, N-diethyl nonyl amine, N, N-diethyl decyl amine, N, N-diethyl undecylamine, N, N-diethyl lauryl amine, N, N-diethyl tridecyl amine, N, N-diethyl tetradecy lamine as preferably, can relate to the tertiary amine with 10-14 carbon atom long-chain alkyl.

Quaternary ammonium salt by general formula (1) representative can be prepared with the quaternizing agent reaction of being represented by following general formula (12) by making the tertiary amine by following general formula (11) representative.

R wherein ₂And R ₃Represent the 1-2 carbon atom alkyl separately;

R ₁-X (12)

R wherein ₁Represent the 8-14 carbon atom alkyl, X represents chlorine atom, bromine atoms or iodine atom.

As the tertiary amine of above-mentioned general formula (11), the example that can relate to has 1,2-two (N, the N-dimethylaminomethyl) benzene, 1,3-two (N, N-dimethylaminomethyl) benzene, 1,4-two (N, the N-dimethylaminomethyl) benzene, 1,2-two (N, N-diethyl amino methyl) benzene, 1,3-two (N, N-diethyl amino methyl) benzene, 1,4-two (N, N-diethyl amino methyl) benzene.Examples of compounds as above-mentioned general formula (12), can relate to alkyl halide, as octyl group chlorine, nonyl chlorine, decyl chloride, undecyl chlorine, dodecyl chloride, tridecyl chlorine, myristyl chlorine, n-octyl bromide, nonyl bromine, decyl bromide, undecyl bromine, dodecyl bromide, tridecyl bromine, myristyl bromine, n octyl iodide, nonyl iodine, iododecane, undecyl iodine, dodecyl iodine, tridecyl iodine, myristyl iodine, as preferably, can relate to the alkyl halide that has 10-14 carbon atom in the alkyl.

Quaternary ammonium salt by general formula (1) representative also can be prepared with the quaternizing agent reaction of being represented by following general formula (14) by making the tertiary amine by following general formula (13) representative.

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂Represent the 1-2 carbon atom alkyl;

R ₃-Y (14)

R wherein ₃Represent the 1-2 carbon atom alkyl, the group that Y represents chlorine atom, bromine atoms, iodine atom or represented by following general formula (15), (16), (17) weary.

R wherein ₈Represent the 1-2 carbon atom alkyl;

R wherein ₉And R ₁₀Represent hydrogen atom or methyl separately;

R wherein ₁₁Represent the 1-2 carbon atom alkyl.

As tertiary amine example by above-mentioned general formula (13) representative, can relate to 1,2-two (N-octyl group-N-methyl aminomethyl) benzene, 1,2-two (N-octyl group-N-ethyl aminomethyl) benzene, 1,2-two (N-nonyl-N-methyl aminomethyl) benzene, 1,2-two (N-nonyl-N-ethyl aminomethyl) benzene, 1,2-two (N-decyl-N-methyl aminomethyl) benzene, 1,2-two (N-decyl-N-ethyl aminomethyl) benzene, 1,2-two (N-undecyl-N-methyl aminomethyl) benzene, 1,2-two (N-undecyl-N-ethyl aminomethyl) benzene, 1,2-two (N-dodecyl-N-methyl aminomethyl) benzene, 1,2-two (N-dodecyl-N-ethyl aminomethyl) benzene, 1,2-two (N-tridecyl-N-methyl aminomethyl) benzene, 1,2-two (N-tridecyl-N-ethyl aminomethyl) benzene, 1,2-two (N-myristyl-N-methyl aminomethyl) benzene, 1,2-two (N-myristyl-N-ethyl aminomethyl) benzene, 1,3-two (N-octyl group-N-methyl aminomethyl) benzene, 1,3-two (N-octyl group-N-ethyl aminomethyl) benzene, 1,3-two (N-nonyl-N-methyl aminomethyl) benzene, 1,3-two (N-nonyl-N-ethyl aminomethyl) benzene, 1,3-two (N-decyl-N-methyl aminomethyl) benzene, 1,3-two (N-decyl-N-ethyl aminomethyl) benzene, 1,3-two (N-undecyl-N-methyl aminomethyl) benzene, 1,3-two (N-undecyl-N-ethyl aminomethyl) benzene, 1,3-two (N-dodecyl-N-methyl aminomethyl) benzene, 1,3-two (N-dodecyl-N-ethyl aminomethyl) benzene, 1,3-two (N-tridecyl-N-methyl aminomethyl) benzene, 1,3-two (N-tridecyl-N-ethyl aminomethyl) benzene, 1,3-two (N-myristyl-N-methyl aminomethyl) benzene, 1,3-two (N-myristyl-N-ethyl aminomethyl) benzene, 1,4-two (N-octyl group-N-methyl aminomethyl) benzene, 1,4-two (N-octyl group-N-ethyl aminomethyl) benzene, 1,4-two (N-nonyl-N-methyl aminomethyl) benzene, 1,4-two (N-nonyl-N-ethyl aminomethyl) benzene, 1,4-two (N-decyl-N-methyl aminomethyl) benzene, 1,4-two (N-decyl-N-ethyl aminomethyl) benzene, 1,4-two (N-undecyl-N-methyl aminomethyl) benzene, 1,4-two (N-undecyl-N-ethyl aminomethyl) benzene, 1,4-two (N-dodecyl-N-methyl aminomethyl) benzene, 1,4-two (N-dodecyl-N-ethyl aminomethyl) benzene, 1,4-two (N-tridecyl-N-methyl aminomethyl) benzene, 1,4-two (N-tridecyl-N-ethyl aminomethyl) benzene, 1,4-two (N-myristyl-N-methyl aminomethyl) benzene, 1,4-two (N-myristyl-N-ethyl aminomethyl) benzene, as preferably, can relate to tertiary amine with 10-14 carbon atom long-chain alkyl.As the examples of compounds of general formula (14), can relate to alkyl halide, as methyl chloride, ethyl chloride, methyl bromide, bromic ether, methyl iodide, ethyl iodide; Dialkyl group sulfuric acid is as dimethyl sulfate, diethyl sulfuric acid; Alkyl sulfonate esters is as methyl tosylate, ethyl p-toluenesulfonate; And trialkylphosphate, as trimethyl phosphate, triethyl phosphate.

Quaterisation solvent as these tertiary amines and quaternizing agent, preferred water, a kind of alcohol or the mixed solvent of the two, as alcohol, particular methanol, ethanol, normal propyl alcohol, isopropyl alcohol, n-butanol, sec-butyl alcohol, isobutanol and the tert-butyl alcohol, but reaction dissolvent is not limited to these.Reaction temperature will depend on the alkyl chain length of tertiary amine or quaternizing agent, but under 80 ℃ or higher temperature, reaction is carried out more usually.

Quaternary ammonium salt by general formula (1) representative can be prepared by ion-exchange, carry out that two kinds of compounds of ion exchange are a kind of to be the quarternary ammonium salt compound that contains cation group of following general formula (18), another kind is the compound of one of sulfuric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, nitric acid, nitrous acid, chloric acid, chlorous acid, hypochlorous acid or general formula (19), (20), (21), (22), (23).

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₇And R ₈Represent the 1-2 carbon atom alkyl separately;

R ₄-COOH (19)

R wherein ₄Represent 1-7 carbon atom alkyl or alkenyl, this alkyl or alkenyl can have a hydroxyl or carbonyl;

HOOC-R ₅-COOH (20)

R wherein ₅Represent direct key or 1-8 carbon atom alkylidene or alkenylene, this alkylidene or alkenylene can have a hydroxyl;

Each R wherein ₆Represent the 1-8 carbon atom alkyl, phosphate can be monoesters, diester or the mixture of the two;

Each R wherein ₇Represent the 1-8 carbon atom alkyl, phosphate can be monoesters, diester or the mixture of the two;

R wherein ₉And R ₁₀Represent hydrogen atom, methyl or carboxyl separately.

Examples of compounds as above-mentioned general formula (19), can relate to carboxylic acid, as acetate, propionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, caproic acid, sad, lactic acid, pyruvic acid, acetoacetate, acrylic acid and methacrylate, wherein preferred carboxylic acid can relate to acetate, propionic acid, butyric acid, isobutyric acid, lactic acid and acetoacetate.

Examples of compounds as general formula (20), can relate to dicarboxylic acids, as ethanedioic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, decanedioic acid, tartaric acid, maleic acid and fumaric acid, wherein preferred dicarboxylic acids can relate to malonic acid, tartaric acid and maleic acid.

Phosphate compound example as general formula (21), can relate to monoesters and diester with 1-8 carbon atom alkyl, the alkyl that preferred monoesters and diester can relate to wherein is methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, sec-butyl or the tert-butyl group.

Phosphate compound example as general formula (22), can relate to monoesters and diester with 1-8 carbon atom alkyl, the alkyl that preferred monoesters and diester can relate to wherein is methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl group, sec-butyl or the tert-butyl group.

As the examples of compounds of general formula (23), preferably use sulfonic acid, as o-toluene sulfonic acid, m-toluene sulfonic acid, p-methyl benzenesulfonic acid, ortho-xylene-4-sulfonic acid ,-dimethylbenzene-4-sulfonic acid, right-xylene monosulfonic acid and different naphthalene sulfonic acids.

Use the anion exchange resin packed column can make ion exchange be easy to carry out.

The present invention will be further specified by the following example, and but, the present invention can not limited by these embodiment by any way.

Embodiment 1

After in 500 milliliters of reaction vessels, adding 42.6 gram domiphens and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-ortho-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained dichloride 1, add water in 2-two (N, the N-dimethyl-N-dodecyl aminomethyl) benzene behind the steaming, transferring to concentration is 10 weight %.It as target compound, is used ¹The H-nuclear magnetic resonance spectroscopy (hereinafter to be referred as ¹H-NMR.Measuring instrument: FT-NMR R-1900, produce in the Hitachi laboratory) differentiate that the result analyzes (Fig. 1) with the 2% heavy methanol solution that contains the tetramethylsilane indicator.

Embodiment 2

After in 500 milliliters of reaction vessels, adding 42.6 gram domiphens and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-meta-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 3

After in 500 milliliters of reaction vessels, adding 42.6 gram domiphens and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-paraxylene is dissolved in the solution of 200 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Behind the steaming,, filter the crystallization that collecting precipitation comes out, and use cold water washing refining solution cooling.Gained dichloride 1,4-two (N, N-dimethyl-N-dodecyl aminomethyl) benzene crystallization is dissolved in water, and transferring to concentration is 1 weight %.It as target compound, is used ¹H-NMR differentiates, interpretation of result (Fig. 2).

Embodiment 4

After in 500 milliliters of reaction vessels, adding 48.2 gram myristyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-ortho-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 2-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 5

After in 500 milliliters of reaction vessels, adding 48.2 gram myristyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-meta-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 5 weight %.

Embodiment 6

After in 500 milliliters of reaction vessels, adding 48.2 gram myristyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-paraxylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.With refining solution cooling, filter the crystallization that collecting precipitation comes out, and use cold water washing behind the steaming.With gained dichloride 1,4-two (N, N-dimethyl-N-myristyl aminomethyl) benzene crystallization is dissolved in water, and transferring to concentration is 1 weight %.

Embodiment 7

After in 500 milliliters of reaction vessels, adding 37.0 gram decyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-ortho-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 2-two (N, N-dimethyl-N-decyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 8

After in 500 milliliters of reaction vessels, adding 37.0 gram decyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-meta-xylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-decyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 5 weight %.

Embodiment 9

After in 500 milliliters of reaction vessels, adding 37.0 gram decyl dimethylamine and 50 ml waters, this mixture is heated to 75 ℃.Then, slowly drip 17.5 gram α, α '-two chloro-paraxylene is dissolved in the solution of 100 milliliters of isopropyl alcohols.Dropwise, add hot reflux and reacted in one hour, obtain a transparent homogeneous phase solution.After the slaking 2 hours, to solution in slowly add 200 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.With refining solution cooling, filter the crystallization that collecting precipitation comes out, and use cold water washing behind the steaming.With gained dichloride 1,4-two (N, N-dimethyl-N-decyl aminomethyl) benzene crystallization is dissolved in water, and transferring to concentration is 1 weight %.

Embodiment 10

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 2-two (N, N-dimethyl-aminomethyl) benzene, 35.3 gram decyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 2 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 2-two (N, N-dimethyl-N-decyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 11

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 3-two (N, N-dimethyl-aminomethyl) benzene, 35.3 gram decyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 2 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-decyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 5 weight %.

Embodiment 12

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 4-two (N, N-dimethyl-aminomethyl) benzene, 35.3 gram decyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 2 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 4-two (N, N-dimethyl-N-decyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 1 weight %.

Embodiment 13

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 2-two (N, N-dimethyl-aminomethyl) benzene, 40.9 gram dodecyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 14

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 3-two (N, N-dimethyl-aminomethyl) benzene, 40.9 gram dodecyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene dichloride product behind the steaming, transferring to dense giving up is 5 weight %.

Embodiment 15

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 4-two (N, N-dimethyl-aminomethyl) benzene, 40.9 gram dodecyl chlorides, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 2 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 1 weight %.

Embodiment 16

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 2-two (N, N-dimethyl-aminomethyl) benzene, 46.5 gram myristyl chlorine, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 3 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 2-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 10 weight %.

Embodiment 17

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 3-two (N, N-dimethyl-aminomethyl) benzene, 46.5 gram myristyl chlorine, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 3 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 3-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 5 weight %.

Embodiment 18

In 500 milliliters of reaction vessels, add 17.8 grams 1, behind 4-two (N, N-dimethyl-aminomethyl) benzene, 46.5 gram myristyl chlorine, 50 ml waters and the 200 milliliters of isopropyl alcohols, add hot reflux and it was reacted in 3 hours, obtain a transparent homogeneous phase solution.After the slaking 3 hours, slowly add 300 ml waters on one side, carry out steaming on one side, remove alcohol moiety with distillation.Again to gained 1, add water in 4-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene dichloride product behind the steaming, transferring to concentration is 1 weight %.

Embodiment 19

The compound that obtains among the embodiment 7 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-decyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 20

The compound that obtains among the embodiment 8 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-decyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 21

The compound that obtains among the embodiment 9 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-decyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 22

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 23

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 24

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 25

The compound that obtains among the embodiment 4 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-myristyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 26

The compound that obtains among the embodiment 5 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-myristyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 27

The compound that obtains among the embodiment 6 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with methyl orthophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-myristyl aminomethyl) the benzenephosphonic acid methyl esters salt product, and transferring to concentration is 1 weight %.

Embodiment 28

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with etherophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid ethyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 29

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with etherophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid ethyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 30

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with etherophosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid ethyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 31

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with phosphoric acid propyl ester (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid propyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 32

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with phosphoric acid propyl ester (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid propyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 33

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH6.8 ± 0.2 with phosphoric acid propyl ester (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid propyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 34

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.3 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 35

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.3 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 36

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.3 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.It as target compound, is used ¹H-NMR differentiates, interpretation of result (Fig. 3).

Embodiment 37

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with the own ester of phosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the own ester salt of the benzenephosphonic acid product, and transferring to concentration is 1 weight %.

Embodiment 38

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with the own ester of phosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the own ester salt of the benzenephosphonic acid product, and transferring to concentration is 1 weight %.

Embodiment 39

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with the own ester of phosphoric acid (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the own ester salt of the benzenephosphonic acid product, and transferring to concentration is 1 weight %.

Embodiment 40

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with tartaric acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene tartrate product, and transferring to concentration is 1 weight %.

Embodiment 41

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with succinic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the diphenyl succinic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 42

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with malonic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylmalonate salt product, and transferring to concentration is 1 weight %.

Embodiment 43

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with adipic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene adipate product, and transferring to concentration is 1 weight %.

Embodiment 44

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with acetate, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylacetate product, and transferring to concentration is 1 weight %.

Embodiment 45

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with lactic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenyllactic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 46

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene gluconate product, and transferring to concentration is 1 weight %.

Embodiment 47

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with tartaric acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene tartrate product, and transferring to concentration is 1 weight %.

Embodiment 48

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with succinic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the diphenyl succinic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 49

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with malonic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylmalonate salt product, and transferring to concentration is 1 weight %.

Embodiment 50

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with adipic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene adipate product, and transferring to concentration is 1 weight %.

Embodiment 51

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with acetate, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylacetate product, and transferring to concentration is 1 weight %.

Embodiment 52

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains is transferred pH7.0 ± 0.5 with lactic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenyllactic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 53

The compound that obtains among the embodiment 3 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene gluconate product, and transferring to concentration is 1 weight %.

Embodiment 54

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with tartaric acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene tartrate product, and transferring to concentration is 1 weight %.

Embodiment 55

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with succinic acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the diphenyl succinic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 56

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with malonic acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylmalonate salt product, and transferring to concentration is 1 weight %.

Embodiment 57

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with adipic acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene adipate product, and transferring to concentration is 1 weight %.

Embodiment 58

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with acetate, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylacetate product, and transferring to concentration is 1 weight %.

Embodiment 59

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with lactic acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenyllactic acid salt product, and transferring to concentration is 1 weight %.

Embodiment 60

The compound that obtains among the embodiment 2 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 3-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene gluconate product, and transferring to concentration is 1 weight %.

Embodiment 61

The compound that obtains among the embodiment 7 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-decyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 62

The compound that obtains among the embodiment 9 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-decyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 63

The compound that obtains among the embodiment 4 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 2-two (N, N-dimethyl-N-myristyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 64

The compound that obtains among the embodiment 6 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with butylphosphoric acid ester (monoesters/diester=50/50), again to gained 1, adds water in 4-two (N, N-dimethyl-N-myristyl aminomethyl) the benzenephosphonic acid butyl ester salt product, and transferring to concentration is 1 weight %.

Embodiment 65

The compound that obtains among the embodiment 7 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-decyl aminomethyl) the benzene gluconate salt product, and transferring to concentration is 1 weight %.

Embodiment 66

The compound that obtains among the embodiment 9 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-decyl aminomethyl) the benzene gluconate salt product, and transferring to concentration is 1 weight %.

Embodiment 67

The compound that obtains among the embodiment 4 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene gluconate salt product, and transferring to concentration is 1 weight %.

Embodiment 68

The compound that obtains among the embodiment 6 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.5 with gluconic acid, again to gained 1, adds water in 4-two (N, N-dimethyl-N-myristyl aminomethyl) the benzene gluconate salt product, and transferring to concentration is 1 weight %.

Embodiment 69

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.2 with sulfuric acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the phenylsulfate product, and transferring to concentration is 1 weight %.

Embodiment 70

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.2 with nitric acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene nitrate product, and transferring to concentration is 1 weight %.

Embodiment 71

The compound that obtains among the embodiment 1 is made with extra care with anion exchange resin.The refining solution that obtains transfers to pH7.0 ± 0.2 with p-methyl benzenesulfonic acid, again to gained 1, adds water in 2-two (N, N-dimethyl-N-dodecyl aminomethyl) the benzene tosilate product, and transferring to concentration is 1 weight %.

Comparative Examples 1

Benzalkonium chloride.

Comparative Examples 2

Didextrose acid chlohexidine.

Evaluation method

According to Japanese chemotherapy association standard, measure the fixedness minimal bactericidal concentration (MBC) partly of the compound of embodiment 1 to 71 and Comparative Examples 1 to 2, use the methicillin-resistant staphylococcus aureus (S.aureus (MRSA)) of 2 bacterial strains during measurement, the staphylococcus aureus of 2 bacterial strains (S.aureus), the Escherichia coli of 3 bacterial strains (E.coli), the Pseudomonas aeruginosa of 3 bacterial strains (P.aeruginosa), the pneumobacillus of 2 bacterial strains (K.pneumoniae), the serratia marcesens of 2 bacterial strains (S.marcescens), with the Salmonella enteritidis (S.enteritidis) of 2 bacterial strains, and compare their bactericidal effect.The results are shown in Table 1 to 19.

Table 1

Bacterial strain	MBC (mcg/ml)
					Comparative Examples 1	Comparative Examples 2	Embodiment 1	Embodiment 2
	Staphylococcus aureus (MRSA) A	50	25	2.5					2.5
Staphylococcus aureus (MRSA) B					50	25	2.5	2.5
	Staphylococcus aureus A	25	25	2.5					2.5
Staphylococcus aureus B					25	50	2.5	2.5
	Escherichia coli A	25	5	2.5					2.5
Escherichia coli B					25	10	2.5	2.5
	Escherichia coli C	25	10	2.5					2.5
Pseudomonas aeruginosa A					25	25	2.5	2.5
	Pseudomonas aeruginosa B	50	25	2.5					2.5
Pseudomonas aeruginosa C					50	100	2.5	2.5
	Pneumobacillus A	50	5	5					5
Pneumobacillus B					50	5	5	5
	Serratia marcesens A	25	25	5					5
Serratia marcesens B					25	10	5	5
	Salmonella enteritidis A	25	5	5					5
Salmonella enteritidis B					25	5	5	5

Table 2

Bacterial strain	MBC (mcg/ml)
					Embodiment 3	Embodiment 4	Embodiment 5	Embodiment 6
	Staphylococcus aureus (MRSA) A	2.5	10	5					10
Staphylococcus aureus (MRSA) B					2.5	5	10	5
	Staphylococcus aureus A	2.5	5	5					5
Staphylococcus aureus B					2.5	5	5	5
	Escherichia coli A	2.5	5	5					5
Escherichia coli B					2.5	5	10	5
	Escherichia coli C	2.5	10	5					10
Pseudomonas aeruginosa A					2.5	25	25	25
	Pseudomonas aeruginosa B	2.5	5	5					5
Pseudomonas aeruginosa C					2.5	5	5	5
	Pneumobacillus A	5	25	10					25
Pneumobacillus B					5	10	25	10
	Serratia marcesens A	5	10	10					10
Serratia marcesens B					5	10	10	10
	Salmonella enteritidis A	5	5	10					10
Salmonella enteritidis B					5	5	10	10

Table 3

Bacterial strain	MBC (mcg/ml)
					Embodiment 7	Embodiment 8	Embodiment 9	Embodiment 10
	Staphylococcus aureus (MRSA) A	10	10	10					10
Staphylococcus aureus (MRSA) B					10	10	10	10
	Staphylococcus aureus A	25	25	25					25
Staphylococcus aureus B					25	25	25	25
	Escherichia coli A	25	25	25					25
Escherichia coli B					25	25	25	25
	Escherichia coli C	25	25	25					25
Pseudomonas aeruginosa A					10	10	10	25
	Pseudomonas aeruginosa B	25	25	25					25
Pseudomonas aeruginosa C					10	10	10	25
	Pneumobacillus A	25	25	25					25
Pneumobacillus B					25	25	25	25
	Serratia marcesens A	50	50	50					50
Serratia marcesens B					50	50	50	50
	Salmonella enteritidis A	50	50	50					50
Salmonella enteritidis B					50	50	50	50

Table 4

Bacterial strain	MBC (mcg/ml)
					Embodiment 11	Embodiment 12	Embodiment 13	Embodiment 14
	Staphylococcus aureus (MRSA) A	10	10	2.5					2.5
Staphylococcus aureus (MRSA) B					10	10	2.5	2.5
	Staphylococcus aureus A	25	25	2.5					2.5
Staphylococcus aureus B					25	25	2.5	2.5
	Escherichia coli A	25	25	2.5					2.5
Escherichia coli B					25	25	2.5	2.5
	Escherichia coli C	25	25	2.5					2.5
Pseudomonas aeruginosa A					25	25	2.5	2.5
	Pseudomonas aeruginosa B	25	25	2.5					2.5
Pseudomonas aeruginosa C					25	25	2.5	2.5
	Pneumobacillus A	25	25	5					5
Pneumobacillus B					25	25	5	5
	Serratia marcesens A	50	50	5					5
Serratia marcesens B					50	50	5	5
	Salmonella enteritidis A	50	50	5					5
Salmonella enteritidis B					50	50	5	5

Table 5

Bacterial strain	MBC (mcg/ml)
					Embodiment 15	Embodiment 16	Embodiment 17	Embodiment 18
	Staphylococcus aureus (MRSA) A	2.5	10	10					10
Staphylococcus aureus (MRSA) B					2.5	10	10	10
	Staphylococcus aureus A	2.5	5	5					5
Staphylococcus aureus B					2.5	5	5	5
	Escherichia coli A	2.5	5	5					5
Escherichia coli B					2.5	10	10	10
	Escherichia coli C	2.5	5	5					5
Pseudomonas aeruginosa A					2.5	5	5	5
	Pseudomonas aeruginosa B	2.5	25	25					25
Pseudomonas aeruginosa C					2.5	5	5	5
	Pneumobacillus A	5	25	25					25
Pneumobacillus B					5	10	10	10
	Serratia marcesens A	5	10	10					10
Serratia marcesens B					5	10	10	10
	Salmonella enteritidis A	5	10	10					10
Salmonella enteritidis B					5	10	10	10

Table 6

Bacterial strain	MBC (mcg/ml)
					Embodiment 19	Embodiment 20	Embodiment 21	Embodiment 22
	Staphylococcus aureus (MRSA) A	10	10	10					2.5
Staphylococcus aureus (MRSA) B					10	10	10	2.5
	Staphylococcus aureus A	25	25	25					2.5
Staphylococcus aureus B					25	25	25	2.5
	Escherichia coli A	25	25	25					2.5
Escherichia coli B					25	25	25	2.5
	Escherichia coli C	25	25	25					2.5
Pseudomonas aeruginosa A					25	25	25	2.5
	Pseudomonas aeruginosa B	25	25	25					2.5
Pseudomonas aeruginosa C					25	25	25	2.5
	Pneumobacillus A	25	25	25					5
Pneumobacillus B					25	25	25	5
	Serratia marcesens A	50	50	50					5
Serratia marcesens B					50	50	50	5
	Salmonella enteritidis A	50	50	50					5
Salmonella enteritidis B					50	50	50	5

Table 7

Bacterial strain	MBC (mcg/ml)
					Embodiment 23	Embodiment 24	Embodiment 25	Embodiment 26
	Staphylococcus aureus (MRSA) A	2.5	2.5	10					10
Staphylococcus aureus (MRSA) B					2.5	2.5	10	10
	Staphylococcus aureus A	2.5	2.5	5					5
Staphylococcus aureus B					2.5	2.5	5	5
	Escherichia coli A	2.5	2.5	5					5
Escherichia coli B					2.5	2.5	10	10
	Escherichia coli C	2.5	2.5	5					5
Pseudomonas aeruginosa A					2.5	2.5	5	5
	Pseudomonas aeruginosa B	2.5	2.5	25					25
Pseudomonas aeruginosa C					2.5	2.5	5	5
	Pneumobacillus A	5	5	25					25
Pneumobacillus B					5	5	10	10
	Serratia marcesens A	5	5	10					10
Serratia marcesens B					5	5	10	10
	Salmonella enteritidis A	5	5	10					10
Salmonella enteritidis B					5	5	10	10

Table 8

Bacterial strain	MBC (mcg/ml)
					Embodiment 27	Embodiment 28	Embodiment 29	Embodiment 30
	Staphylococcus aureus (MRSA) A	10	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					10	2.5	2.5	2.5
	Staphylococcus aureus A	5	2.5	2.5					2.5
Staphylococcus aureus B					5	5	2.5	5
	Escherichia coli A	5	2.5	2.5					2.5
Escherichia coli B					10	2.5	2.5	2.5
	Escherichia coli C	5	2.5	2.5					2.5
Pseudomonas aeruginosa A					5	5	5	5
	Pseudomonas aeruginosa B	25	5	5					5
Pseudomonas aeruginosa C					5	5	5	5
	Pneumobacillus A	25	5	5					5
Pneumobacillus B					10	5	5	5
	Serratia marcesens A	10	5	5					5
Serratia marcesens B					10	5	5	5
	Salmonella enteritidis A	10	5	5					5
Salmonella enteritidis B					10	5	5	5

Table 9

Bacterial strain	MBC (mcg/ml)
					Embodiment 31	Embodiment 32	Embodiment 33	Embodiment 34
	Staphylococcus aureus (MRSA) A	2.5	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					2.5	2.5	2.5	2.5
	Staphylococcus aureus A	5	2.5	5					5
Staphylococcus aureus B					5	2.5	5	5
	Escherichia coli A	2.5	2.5	5					2.5
Escherichia coli B					2.5	2.5	5	2.5
	Escherichia coli C	2.5	2.5	5					2.5
Pseudomonas aeruginosa A					5	5	5	5
	Pseudomonas aeruginosa B	5	5	5					5
Pseudomonas aeruginosa C					5	5	5	5
	Pneumobacillus A	5	5	5					5
Pneumobacillus B					5	5	5	5
	Serratia marcesens A	5	5	5					5
Serratia marcesens B					5	5	5	5
	Salmonella enteritidis A	5	5	5					5
Salmonella enteritidis B					5	5	5	5

Table 10

Bacterial strain	MBC (mcg/ml)
					Embodiment 35	Embodiment 36	Embodiment 37	Embodiment 38
	Staphylococcus aureus (MRSA) A	2.5	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					2.5	2.5	2.5	2.5
	Staphylococcus aureus A	2.5	2.5	5					2.5
Staphylococcus aureus B					2.5	2.5	5	2.5
	Escherichia coli A	2.5	5	2.5					2.5
Escherichia coli B					2.5	5	2.5	2.5
	Escherichia coli C	2.5	5	2.5					2.5
Pseudomonas aeruginosa A					5	5	5	5
	Pseudomonas aeruginosa B	5	5	5					5
Pseudomonas aeruginosa C					5	5	5	5
	Pneumobacillus A	2.5	5	5					5
Pneumobacillus B					2.5	5	5	5
	Serratia marcesens A	2.5	5	5					5
Serratia marcesens B					2.5	5	5	5
	Salmonella enteritidis A	5	5	5					5
Salmonella enteritidis B					5	5	5	5

Table 11

Bacterial strain	MBC (mcg/ml)
					Embodiment 39	Embodiment 40	Embodiment 41	Embodiment 42
	Staphylococcus aureus (MRSA) A	2.5	2.5	5					2.5
Staphylococcus aureus (MRSA) B					2.5	2.5	5	2.5
	Staphylococcus aureus A	2.5	5	5					2.5
Staphylococcus aureus B					2.5	5	5	2.5
	Escherichia coli A	5	5	5					2.5
Escherichia coli B					5	5	5	2.5
	Escherichia coli C	5	5	5					2.5
Pseudomonas aeruginosa A					5	10	10	2.5
	Pseudomonas aeruginosa B	5	10	10					5
Pseudomonas aeruginosa C					5	10	10	5
	Pneumobacillus A	5	5	5					5
Pneumobacillus B					5	5	5	2.5
	Serratia marcesens A	5	10	10					5
Serratia marcesens B					5	10	10	5
	Salmonella enteritidis A	5	10	10					5
Salmonella enteritidis B					5	10	10	5

Table 12

Bacterial strain	MBC (mcg/ml)
					Embodiment 43	Embodiment 44	Embodiment 45	Embodiment 46
	Staphylococcus aureus (MRSA) A	2.5	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					2.5	2.5	2.5	2.5
	Staphylococcus aureus A	2.5	2.5	2.5					2.5
Staphylococcus aureus B					2.5	2.5	2.5	2.5
	Escherichia coli A	2.5	2.5	2.5					5
Escherichia coli B					2.5	2.5	2.5	5
	Escherichia coli C	2.5	2.5	2.5					5
Pseudomonas aeruginosa A					2.5	5	5	5
	Pseudomonas aeruginosa B	5	5	5					5
Pseudomonas aeruginosa C					5	5	5	5
	Pneumobacillus A	2.5	2.5	2.5					2.5
Pneumobacillus B					2.5	2.5	2.5	2.5
	Serratia marcesens A	5	5	5					5
Serratia marcesens B					5	5	5	5
	Salmonella enteritidis A	5	5	5					2.5
Salmonella enteritidis B					5	5	5	2.5

Table 13

Bacterial strain	MBC (mcg/ml)
					Embodiment 47	Embodiment 48	Embodiment 49	Embodiment 50
	Staphylococcus aureus (MRSA) A	2.5	5	2.5					2.5
Staphylococcus aureus (MRSA) B					2.5	5	2.5	2.5
	Staphylococcus aureus A	5	5	2.5					2.5
Staphylococcus aureus B					5	5	2.5	2.5
	Escherichia coli A	5	5	2.5					2.5
Escherichia coli B					5	5	2.5	2.5
	Escherichia coli C	5	5	2.5					2.5
Pseudomonas aeruginosa A					10	10	2.5	2.5
	Pseudomonas aeruginosa B	10	10	5					5
Pseudomonas aeruginosa C					10	10	5	5
	Pneumobacillus A	5	5	5					2.5
Pneumobacillus B					5	5	2.5	2.5
	Serratia marcesens A	10	10	5					5
Serratia marcesens B					10	10	5	5
	Salmonella enteritidis A	10	10	5					5
Salmonella enteritidis B					10	10	5	5

Table 14

Bacterial strain	MBC (mcg/ml)
					Embodiment 51	Embodiment 52	Embodiment 53	Embodiment 54
	Staphylococcus aureus (MRSA) A	2.5	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					2.5	2.5	2.5	2.5
	Staphylococcus aureus A	2.5	2.5	5					5
Staphylococcus aureus B					2.5	2.5	5	5
	Escherichia coli A	2.5	2.5	5					5
Escherichia coli B					2.5	2.5	5	5
	Escherichia coli C	2.5	2.5	5					5
Pseudomonas aeruginosa A					5	5	5	10
	Pseudomonas aeruginosa B	5	5	5					10
Pseudomonas aeruginosa C					5	5	5	10
	Pneumobacillus A	2.5	2.5	10					5
Pneumobacillus B					2.5	2.5	5	5
	Serratia marcesens A	5	5	5					10
Serratia marcesens B					5	5	5	10
	Salmonella enteritidis A	5	5	2.5					10
Salmonella enteritidis B					5	5	2.5	10

Table 15

Bacterial strain	MBC (mcg/ml)
					Embodiment 55	Embodiment 56	Embodiment 57	Embodiment 58
	Staphylococcus aureus (MRSA) A	5	2.5	2.5					2.5
Staphylococcus aureus (MRSA) B					5	2.5	2.5	2.5
	Staphylococcus aureus A	5	2.5	2.5					2.5
Staphylococcus aureus B					5	2.5	2.5	2.5
	Escherichia coli A	5	2.5	2.5					2.5
Escherichia coli B					5	2.5	2.5	2.5
	Escherichia coli C	5	2.5	2.5					2.5
Pseudomonas aeruginosa A					10	2.5	2.5	5
	Pseudomonas aeruginosa B	10	5	5					5
Pseudomonas aeruginosa C					10	5	5	5
	Pneumobacillus A	5	5	2.5					2.5
Pneumobacillus B					5	2.5	2.5	2.5
	Serratia marcesens A	10	5	5					5
Serratia marcesens B					10	5	5	5
	Salmonella enteritidis A	10	5	5					5
Salmonella enteritidis B					10	5	5	5

Table 16

Bacterial strain	MBC (mcg/ml)
					Embodiment 59	Embodiment 60	Embodiment 61	Embodiment 62
	Staphylococcus aureus (MRSA) A	2.5	2.5	10					10
Staphylococcus aureus (MRSA) B					2.5	5	10	10
	Staphylococcus aureus A	2.5	5	10					10
Staphylococcus aureus B					2.5	2.5	25	25
	Escherichia coli A	2.5	2.5	25					25
Escherichia coli B					2.5	2.5	25	25
	Escherichia coli C	2.5	2.5	25					25
Pseudomonas aeruginosa A					2.5	2.5	25	25
	Pseudomonas aeruginosa B	5	2.5	25					25
Pseudomonas aeruginosa C					5	5	25	25
	Pneumobacillus A	2.5	5	10					10
Pneumobacillus B					2.5	5	10	10
	Serratia marcesens A	5	2.5	50					50
Serratia marcesens B					5	2.5	50	50
	Salmonella enteritidis A	5	2.5	50					50
Salmonella enteritidis B					5	2.5	50	50

Table 17

Bacterial strain	MBC (mcg/ml)
					Embodiment 63	Embodiment 64	Embodiment 65	Embodiment 66
	Staphylococcus aureus (MRSA) A	5	5	10					10
Staphylococcus aureus (MRSA) B					5	5	10	10
	Staphylococcus aureus A	5	5	10					10
Staphylococcus aureus B					10	10	25	25
	Escherichia coli A	5	5	25					25
Escherichia coli B					5	5	25	25
	Escherichia coli C	5	5	25					25
Pseudomonas aeruginosa A					10	25	25	50
	Pseudomonas aeruginosa B	10	5	25					25
Pseudomonas aeruginosa C					5	10	25	25
	Pneumobacillus A	10	10	10					10
Pneumobacillus B					10	10	25	25
	Serratia marcesens A	25	25	50					50
Serratia marcesens B					25	25	50	50
	Salmonella enteritidis A	10	25	50					50
Salmonella enteritidis B					10	25	50	50

Table 18

Bacterial strain	MBC (mcg/ml)
					Embodiment 67	Embodiment 68	Embodiment 69	Embodiment 70
	Staphylococcus aureus (MRSA) A	5	5	2.5					2.5
Staphylococcus aureus (MRSA) B					5	5	2.5	2.5
	Staphylococcus aureus A	5	5	2.5					2.5
Staphylococcus aureus B					5	5	5	5
	Escherichia coli A	5	5	2.5					2.5
Escherichia coli B					5	5	2.5	2.5
	Escherichia coli C	5	5	2.5					2.5
Pseudomonas aeruginosa A					10	25	5	5
	Pseudomonas aeruginosa B	10	10	5					5
Pseudomonas aeruginosa C					10	10	5	5
	Pneumobacillus A	10	10	5					5
Pneumobacillus B					10	10	5	5
	Serratia marcesens A	25	25	5					5
Serratia marcesens B					25	25	5	5
	Salmonella enteritidis A	25	25	5					5
Salmonella enteritidis B					25	25	5	5

Table 19

Bacterial strain	MBC (mcg/ml)
		Embodiment 71
	Staphylococcus aureus (MRSA) A		5
Staphylococcus aureus (MRSA) B		5
	Staphylococcus aureus A		5
Staphylococcus aureus B		5
	Escherichia coli A		5
Escherichia coli B		5
	Escherichia coli C		5
Pseudomonas aeruginosa A		10
	Pseudomonas aeruginosa B		10
Pseudomonas aeruginosa C		10
	Pneumobacillus A		5
Pneumobacillus B		5
	Serratia marcesens A		10
Serratia marcesens B		10
	Salmonella enteritidis A		10
Salmonella enteritidis B		10

The quaternary ammonium salt that synthesizes according to the present invention demonstrates more powerful bactericidal action than traditional disinfectant benzalkonium chloride, and has quite or bigger bactericidal effect than didextrose acid chlohexidine, therefore can be used as disinfectant or like that.

Claims (6)

1. the quaternary ammonium salt of following general formula (1) representative is as the purposes of disinfectant:

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂And R ₃Represent the 1-2 carbon atom alkyl separately, [B] represents the inorganic or organic anion group of the inorganic of two monovalencies or an organic anion group or a divalence.

2. according to the purposes of claim 1, wherein said inorganic or organic anion group [B] is sulfate ion, phosphate anion, orthophosphite ions, hypophosphite ion, nitrate ion, nitrite ion, chloranion, chlorition, hypochlorite ion or by arbitrary anionic group of following general formula (2)-(8) representative:

2[X ^-] (2)

Wherein X represents chlorine atom, bromine atoms or iodine atom;

2[R ₄COO ^-] (3)

R wherein ₄Represent 1-7 carbon atom alkyl or alkenyl, this alkyl or alkenyl can have a hydroxyl or carbonyl;

[ ^-OCO-R ₅-COO ^-] (4)

R wherein ₅Represent direct key or 1-8 carbon atom alkylidene or alkenylene, this alkylidene or alkenylene can have a hydroxyl;

Each R wherein ₆Represent the 1-8 carbon atom alkyl, the phosphate anion can be simple monoesters or diester, or the mixture of the two;

Each R wherein ₇Represent the 1-8 carbon atom alkyl, the phosphate anion can be simple monoesters or diester, or the mixture of the two;

2[R ₈SO ₄] (7)

R wherein ₈Represent the 1-2 carbon atom alkyl;

R wherein ₉And R ₁₀Represent hydrogen atom, methyl or carboxyl separately.

3. according to the purposes of claim 1 or 2, quaternary ammonium salt wherein uses with can sterilize application carrier or thinner.

4. the preparation method of the described formula of claim 1 (I) quaternary ammonium salt, its compound by making following general formula (11) and the compound of following general formula (12) react synthetic,

R wherein ₂And R ₃Represent the 1-2 carbon atom alkyl separately;

R ₁-X (12)

R wherein ₁Represent the 8-14 carbon atom alkyl, X represents chlorine atom, bromine atoms or iodine atom.

5. the preparation method of the described formula of claim 1 (I) quaternary ammonium salt, its compound by making following general formula (13) and the compound of following general formula (14) react synthetic,

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂Represent the 1-2 carbon atom alkyl;

R ₃-Y (14)

R wherein ₃Represent the 1-2 carbon atom alkyl, the group that Y represents chlorine atom, bromine atoms, iodine atom or represented by one of following general formula (15), (16), (17):

R wherein ₈Represent the 1-2 carbon atom alkyl;

R wherein ₉And R ₁₀Represent hydrogen atom or methyl separately;

R wherein ₁₁Represent the 1-2 carbon atom alkyl.

6. the preparation method of the described formula of claim 1 (I) quaternary ammonium salt, it is by carrying out the ion exchange preparation with the quarternary ammonium salt compound that contains cation group of following general formula (18) with the compound of one of sulfuric acid, phosphoric acid, phosphorous acid, hypophosphorous acid, nitric acid, nitrous acid, chloric acid, chlorous acid, hypochlorous acid or general formula (19), (20), (21), (22), (23)

R wherein ₁Represent the 8-14 carbon atom alkyl, R ₂And R ₃Represent the 1-2 carbon atom alkyl separately;

R ₄-COOH (19)

R wherein ₄Represent 1-7 carbon atom alkyl or alkenyl, this alkyl or alkenyl can have a hydroxyl or carbonyl;

HOOC-R ₅-COOH (20)

R wherein ₅Represent direct key or 1-8 carbon atom alkylidene or alkenylene, this alkylidene or alkenylene can have a hydroxyl;

Each R wherein ₆Represent the 1-8 carbon atom alkyl, phosphate can be monoesters, diester or the mixture of the two;

Each R wherein ₇Represent the 1-8 carbon atom alkyl, phosphate can be monoesters, diester or the mixture of the two;

R wherein ₉And R ₁₀Represent hydrogen atom, methyl or carboxyl separately.

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